Winsted, CT 55+ active adult communities & homes for sale

78 communities near Winsted

Sort by:

Relevance

3.6 rating (7 reviews)

Heritage Village

$100Ks - $500Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

3 rating (2 reviews)

Heritage Hills

$300Ks - $900Ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

4 rating (1 reviews)

Jefferson Village

$200Ks - $500Ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

The Village at Oxford Gre...

$600Ks - $700Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

Want to learn more about 55+ communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

Want to learn more about 55+ rental communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

Rivington

$400Ks - $800Ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

The Retreat at Carmel

$400Ks - $700Ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

Fairview at Oxford Greens

$600Ks - $700Ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

Regency at Woodbridge

$600Ks - $700Ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

Regency at Fishkill

$400Ks - $500Ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Spring Lake Village

$200Ks - $300Ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

4.9 rating (14 reviews)

Chatfield Farms

$500Ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

South Pond Village

$200Ks - $400Ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

Want to learn more about 55+ communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

The Village at Whispering...

$400Ks

The Village at Whispering...Rotterdam, NY

New Construction | 55+ age-restricted | Built 2025 - present | 85 homes

5 rating (1 reviews)

Newtown Woods

$400Ks - $500Ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

Want to learn more about 55+ rental communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

Granite Woods

$600Ks - $700Ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

Bartlett Hill

$500Ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

Evergreen

$500Ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

Baldwin Station

$400Ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

Liberty at Newtown

$300Ks - $400Ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

The Gardens of Wilbraham

$500Ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

Want to learn more about 55+ communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

5 rating (1 reviews)

Paris Square

$400Ks - $700Ks

Paris Square, Northvale, NJ

New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes

Glassbury Court at Cold S...

$500Ks - $700Ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes

Regency at Wappinger

$600Ks - $700Ks

Regency at Wappinger, Wappingers Falls, NY

Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes

Glassbury Court at Hunter...

$500Ks - $700Ks

Glassbury Court at Hunter..., Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes

Want to learn more about 55+ rental communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes

Billingsgate

$400Ks - $600Ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes

Boulder Brook

$200Ks

Boulder Brook, Prospect, CT

Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes

Gloria Commons

$400Ks

Gloria Commons, Milford, CT

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes

Hopmeadow Place

$200Ks - $300Ks

Hopmeadow Place, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes

Want to learn more about 55+ communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

Long Hill Village

$300Ks - $400Ks

Long Hill Village, Trumbull, CT

Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes

Oak Meadow Estates

$400Ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

Park Glen

$600Ks

Park Glen, New Milford, CT

Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes

RiverBend Estates

$400Ks

RiverBend Estates, Oxford, CT

New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes

Summer Wind Estates

$300Ks - $400Ks

Summer Wind Estates, North Haven, CT

New Construction | 55+ age-restricted | Built 2015 - present | 18 homes

Want to learn more about 55+ rental communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

The Woods at Dunham Pond

$400Ks - $500Ks

The Woods at Dunham Pond, New Fairfield, CT

Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes

Regency Meadows

$500Ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes

Bidwell Village

$300Ks - $400Ks

Bidwell Village, Coventry, CT

New Construction | 55+ age-restricted | Built 2020 - present | 37 homes

Want to learn more about 55+ communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

Cobblestone Court

$400Ks - $500Ks

Cobblestone Court, Essex, CT

New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes

Forest Mews

$300Ks - $400Ks

Forest Mews, Avon, CT

Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes

1...2

New Heritage Village

745 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$325,000

2 beds

2 baths

1,432 sq ft

Condo

745 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Oronoque Village

445 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$644,900

1 beds

3 baths

1,620 sq ft

Condo

445 NORTH TRL A, STRATFORD, CT, 06614

909 TILLINGHAST DR # 909, OXFORD, CT, 06...

Community: Fairview at Oxford Greens

Want to learn more about 55+ communities in Winsted, CT? 55places can help!

882 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

Want to learn more about 55+ communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

The Retreat at Carmel

18 WHEELER CT, CARMEL, NY, 10512, Carmel, NY 10512

$749,900

2 beds

3 baths

2,035 sq ft

Condo

18 WHEELER CT, CARMEL, NY, 10512

Community: The Retreat at Carmel

The Village at Oxford Greens

117 COUNTRY CLUB DR # 117, OXFORD, CT, 0..., Oxford, CT 06478

$649,900

3 beds

3 baths

2,666 sq ft

117 COUNTRY CLUB DR # 117, OXFORD, CT, 0...

Community: The Village at Oxford Greens

Want to learn more about 55+ rental communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

Heritage Hills

578 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589

$450,000

1 beds

2 baths

967 sq ft

Condo

578 HERITAGE HLS D, SOMERS, NY, 10589

Community: Heritage Hills

The Village at Oxford Greens

301 FAIRWAY DR # 301, OXFORD, CT, 06478, Oxford, CT 06478

$619,000

2 beds

2 baths

2,080 sq ft

Condo

301 FAIRWAY DR # 301, OXFORD, CT, 06478

Community: The Village at Oxford Greens

Granite Woods

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$229,000

1 beds

1 baths

889 sq ft

Condo

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762

Community: Granite Woods

Regency at Wappinger

61 FARMINGTON RD, WAPPINGERS FALLS, NY, ..., Wappingers Falls, NY 12590

$775,000

2 beds

2 baths

1,738 sq ft

House

61 FARMINGTON RD, WAPPINGERS FALLS, NY, ...

Community: Regency at Wappinger

Oronoque Village

635 NORTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$420,000

1 beds

3 baths

1,454 sq ft

Condo

635 NORTH TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Heritage Hills

656 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$634,900

2 beds

2 baths

1,296 sq ft

Condo

656 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Want to learn more about 55+ communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

Heritage Village

73 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$195,000

Questions? Call us: (860) 909-8066

Oronoque Village

315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$531,500

$199,900

2 beds

2 baths

1,044 sq ft

Condo

405 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Want to learn more about 55+ rental communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

Oronoque Village

446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614

$635,000

3 beds

3 baths

1,426 sq ft

Condo

446 HAMMERSTONE LN B, STRATFORD, CT, 066...

Community: Oronoque Village

Heritage Hills

182 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$475,000

2 beds

2 baths

1,205 sq ft

Condo

182 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Oronoque Village

151 SOUTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614

$460,000

1 beds

3 baths

1,426 sq ft

Condo

151 SOUTH TRL B, STRATFORD, CT, 06614

Community: Oronoque Village

Want to learn more about 55+ communities in Winsted, CT? 55places can help!

Questions? Call us: (860) 909-8066

The Retreat at Carmel

4 FROST CT, CARMEL, NY, 10512, Carmel, NY 10512

$759,900

2 beds

3 baths

2,035 sq ft

Condo

4 FROST CT, CARMEL, NY, 10512

Community: The Retreat at Carmel

Heritage Village

761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$339,900

2 beds

2 baths

1,063 sq ft

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Frequently Asked Questions

What size 55+ communities are there in Winsted?

In Winsted, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winsted?

The smallest 55+ community in Winsted has 38 homes, the largest has 38 homes, and the average community consists of 38 homes.

Are there gated 55+ communities in Winsted?

No, there are no gated 55+ communities in Winsted.

Want more information about active adult communities around Winsted?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Winsted?

Call us: (860) 909-8066

78 communities

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Feb 04, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Winsted, CT 55+ active adult communities & homes for sale

78 communities near Winsted

134 homes near Winsted

2 beds

2 baths

1,432 sq ft

Condo

1 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

910 sq ft

Condo

3 beds

3 baths

2,596 sq ft

Condo

2 beds

3 baths

2,239 sq ft

Condo

2 beds

3 baths

2,239 sq ft

Condo

2 beds

2 baths

1,071 sq ft

Condo

2 beds

3 baths

1,700 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

3 baths

2,054 sq ft

Condo

2 beds

3 baths

1,550 sq ft

Condo

2 beds

2 baths

1,341 sq ft

Condo

2 beds

3 baths

1,666 sq ft

Condo

2 beds

3 baths

2,035 sq ft

Condo

3 beds

3 baths

2,666 sq ft

1 beds

2 baths

967 sq ft

Condo

2 beds

2 baths

2,080 sq ft

Condo

1 beds

1 baths

889 sq ft

Condo

2 beds

2 baths

1,738 sq ft

House

1 beds

3 baths